1-(4-Nitro-phen-yl)-1H-imidazol-3-ium chloride.

In the title salt, C9H8N3O2(+)·Cl(-), the least-squares planes of the imidazolium and benzene rings are almost coplanar, making a dihedral angle of 4.59 (1)°. In the crystal, the chloride anion links the organic mol-ecules through N-H⋯Cl hydrogen bonds, forming chains that run diagonally across the bc face, which compliment strong C-H⋯O hydrogen bonds between neighbouring mol-ecules. These chains are connected to adjacent chains through two weak C-H⋯Cl inter-actions, resulting in hydrogen-bonded sheets extending along the b and c axes. The absolute structure of the title compound was determined using a Flack x parameter of 0.00 (6) and a Hooft y parameter of 0.03 (2).

Related literature

For the synthesis of the title compound, see: Gnanamgari et al. (2009 ▶); Coberan & Peris (2008 ▶); Singh et al., (2011 ▶). For the structure of imidazole with a bond to phenyl via carbon, see: Gayathri et al. (2010 ▶). For structure of imidazole with a bond to phenyl via nitro­gen, see: Zheng et al. (2011 ▶). For the structure of nitro­phenyl imidazole as a ligand in a complex, see: Singh et al. (2010 ▶, 2011 ▶). For related structures, see: Ishihara et al. (1992 ▶); Scheele et al., (2007 ▶). For our related work in this area, see: Ibrahim et al. (2012 ▶).

Experimental

Crystal data

C9H8N3O2 +·Cl−

M = 225.64

Orthorhombic,

a = 14.6042 (8) Å

b = 12.1781 (7) Å

c = 5.6070 (3) Å

V = 997.21 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 173 K

0.54 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.524, T max = 0.746

20153 measured reflections

2217 independent reflections

2120 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.09

2217 reflections

140 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), Hooft et al. (2010 ▶), Spek (2009 ▶); Hooft parameter = 0.03 (2), 856 Bijvoet pairs

Flack parameter: 0.00 (6)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050878/nr2034sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050878/nr2034Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050878/nr2034Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H8N3O2+·Cl−	F(000) = 464
Mr = 225.64	Dx = 1.503 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9896 reflections
a = 14.6042 (8) Å	θ = 2.2–28.3°
b = 12.1781 (7) Å	µ = 0.37 mm−1
c = 5.6070 (3) Å	T = 173 K
V = 997.21 (10) Å3	Block, colourless
Z = 4	0.54 × 0.16 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	2217 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→19
Tmin = 0.524, Tmax = 0.746	k = −16→16
20153 measured reflections	l = −7→6

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.3302P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2217 reflections	Δρmax = 0.30 e Å−3
140 parameters	Δρmin = −0.22 e Å−3
8 restraints	Absolute structure: Flack (1983), Hooft et al. (2010) and Spek (2009); Hooft parameter = 0.03(2), 856 Bijvoet pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model. The nitrogen-bound H atom was located on a difference Fourier map and refined freely with isotropic parameters.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C2	0.61881 (11)	0.39839 (13)	−0.1020 (3)	0.0241 (5)
H2	0.5556	0.4068	−0.0918	0.029*
C4	0.76184 (13)	0.41464 (15)	−0.2179 (4)	0.0308 (5)
H4	0.8131	0.4368	−0.3039	0.037*
C3	0.76136 (12)	0.34674 (15)	−0.0291 (4)	0.0303 (4)
H3	0.8120	0.3132	0.0402	0.036*
N3	0.54484 (10)	0.08365 (11)	0.8199 (3)	0.0274 (3)
N2	0.67050 (9)	0.33611 (11)	0.0429 (3)	0.0210 (3)
N1	0.67229 (10)	0.44554 (12)	−0.2608 (3)	0.0251 (3)
O1	0.46671 (9)	0.09724 (10)	0.8910 (3)	0.0323 (4)
O2	0.59895 (10)	0.01721 (12)	0.9069 (3)	0.0406 (4)
H1	0.6548 (14)	0.4898 (17)	−0.386 (4)	0.030 (5)*
Cl1	0.88518 (2)	0.09410 (3)	0.84010 (10)	0.02647 (12)
C8	0.57713 (11)	0.14961 (13)	0.6161 (3)	0.0217 (3)
C9	0.66889 (12)	0.14545 (14)	0.5571 (4)	0.0303 (4)
H9	0.7093	0.1022	0.6443	0.036*
C10	0.69939 (11)	0.20704 (13)	0.3655 (4)	0.0300 (4)
H10	0.7608	0.2048	0.3216	0.036*
C5	0.63843 (11)	0.27213 (12)	0.2387 (3)	0.0204 (3)
C6	0.54623 (11)	0.27679 (13)	0.3038 (4)	0.0264 (4)
H6	0.5058	0.3212	0.2196	0.032*
C7	0.51553 (11)	0.21484 (13)	0.4943 (4)	0.0260 (4)
H7	0.4543	0.2170	0.5397	0.031*

	U11	U22	U33	U12	U13	U23
C2	0.0202 (8)	0.0223 (7)	0.0297 (13)	0.0005 (6)	−0.0001 (7)	0.0027 (7)
C4	0.0233 (9)	0.0369 (9)	0.0323 (13)	0.0006 (7)	0.0030 (8)	0.0051 (8)
C3	0.0172 (8)	0.0356 (10)	0.0380 (12)	0.0008 (7)	0.0036 (8)	0.0068 (8)
N3	0.0293 (7)	0.0286 (6)	0.0242 (9)	−0.0071 (5)	−0.0034 (8)	0.0010 (6)
N2	0.0173 (6)	0.0196 (6)	0.0262 (8)	−0.0004 (5)	0.0005 (6)	−0.0007 (6)
N1	0.0247 (7)	0.0232 (6)	0.0274 (8)	−0.0002 (5)	−0.0003 (6)	0.0013 (6)
O1	0.0286 (7)	0.0373 (6)	0.0311 (9)	−0.0060 (5)	0.0047 (6)	0.0014 (6)
O2	0.0347 (7)	0.0438 (8)	0.0432 (10)	−0.0032 (6)	−0.0100 (6)	0.0205 (7)
Cl1	0.01823 (18)	0.02836 (18)	0.0328 (2)	−0.00189 (13)	−0.00026 (19)	0.0061 (2)
C8	0.0231 (8)	0.0202 (7)	0.0219 (9)	−0.0046 (6)	−0.0016 (7)	0.0000 (6)
C9	0.0231 (8)	0.0295 (9)	0.0382 (12)	0.0013 (7)	−0.0040 (8)	0.0089 (8)
C10	0.0161 (7)	0.0326 (8)	0.0415 (12)	0.0018 (6)	−0.0002 (8)	0.0085 (9)
C5	0.0210 (8)	0.0190 (6)	0.0214 (8)	−0.0021 (6)	−0.0001 (6)	−0.0009 (6)
C6	0.0202 (7)	0.0256 (7)	0.0333 (12)	0.0044 (6)	−0.0007 (8)	0.0034 (7)
C7	0.0196 (8)	0.0278 (8)	0.0307 (10)	0.0016 (6)	0.0022 (7)	−0.0005 (7)

C2—N1	1.316 (2)	N1—H1	0.92 (2)
C2—N2	1.343 (2)	C8—C7	1.381 (2)
C2—H2	0.9300	C8—C9	1.381 (2)
C4—C3	1.343 (3)	C9—C10	1.384 (3)
C4—N1	1.382 (2)	C9—H9	0.9300
C4—H4	0.9300	C10—C5	1.388 (2)
C3—N2	1.393 (2)	C10—H10	0.9300
C3—H3	0.9300	C5—C6	1.396 (2)
N3—O1	1.220 (2)	C6—C7	1.382 (3)
N3—O2	1.232 (2)	C6—H6	0.9300
N3—C8	1.474 (2)	C7—H7	0.9300
N2—C5	1.425 (2)
N1—C2—N2	108.78 (15)	C7—C8—C9	122.31 (17)
N1—C2—H2	125.6	C7—C8—N3	119.25 (15)
N2—C2—H2	125.6	C9—C8—N3	118.43 (16)
C3—C4—N1	107.45 (16)	C8—C9—C10	118.58 (16)
C3—C4—H4	126.3	C8—C9—H9	120.7
N1—C4—H4	126.3	C10—C9—H9	120.7
C4—C3—N2	106.90 (16)	C9—C10—C5	120.04 (15)
C4—C3—H3	126.5	C9—C10—H10	120.0
N2—C3—H3	126.5	C5—C10—H10	120.0
O1—N3—O2	124.04 (17)	C10—C5—C6	120.53 (17)
O1—N3—C8	118.59 (14)	C10—C5—N2	119.73 (15)
O2—N3—C8	117.37 (15)	C6—C5—N2	119.73 (15)
C2—N2—C3	107.90 (15)	C7—C6—C5	119.50 (15)
C2—N2—C5	126.14 (14)	C7—C6—H6	120.2
C3—N2—C5	125.95 (15)	C5—C6—H6	120.2
C2—N1—C4	108.96 (16)	C8—C7—C6	119.02 (16)
C2—N1—H1	127.3 (13)	C8—C7—H7	120.5
C4—N1—H1	123.7 (13)	C6—C7—H7	120.5
N1—C4—C3—N2	0.1 (2)	C8—C9—C10—C5	0.7 (3)
N1—C2—N2—C3	0.8 (2)	C9—C10—C5—C6	0.4 (3)
N1—C2—N2—C5	179.69 (15)	C9—C10—C5—N2	179.43 (17)
C4—C3—N2—C2	−0.6 (2)	C2—N2—C5—C10	176.61 (17)
C4—C3—N2—C5	−179.45 (15)	C3—N2—C5—C10	−4.7 (3)
N2—C2—N1—C4	−0.7 (2)	C2—N2—C5—C6	−4.4 (3)
C3—C4—N1—C2	0.4 (2)	C3—N2—C5—C6	174.27 (17)
O1—N3—C8—C7	−7.6 (2)	C10—C5—C6—C7	−0.8 (3)
O2—N3—C8—C7	171.90 (17)	N2—C5—C6—C7	−179.81 (15)
O1—N3—C8—C9	171.10 (16)	C9—C8—C7—C6	1.1 (3)
O2—N3—C8—C9	−9.4 (2)	N3—C8—C7—C6	179.81 (16)
C7—C8—C9—C10	−1.5 (3)	C5—C6—C7—C8	0.0 (3)
N3—C8—C9—C10	179.81 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.92 (2)	2.08 (2)	2.9976 (17)	178 (2)
C9—H9···Cl1	0.93	2.80	3.5898 (19)	144
C2—H2···Cl1ii	0.93	2.52	3.4286 (17)	166
C4—H4···O2i	0.93	2.29	3.181 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.92 (2)	2.08 (2)	2.9976 (17)	178 (2)
C9—H9⋯Cl1	0.93	2.80	3.5898 (19)	144
C2—H2⋯Cl1ii	0.93	2.52	3.4286 (17)	166
C4—H4⋯O2i	0.93	2.29	3.181 (2)	161

Symmetry codes: (i) ; (ii) .